Total synthesis of dysiherbaine

Makoto Sasaki; Nobuyuki Akiyama; Koichi Tsubone; Muneo Shoji; Masato Oikawa; Ryuichi Sakai

doi:10.1016/j.tetlet.2007.05.180

Total synthesis of dysiherbaine

Makoto Sasaki, Nobuyuki Akiyama, Koichi Tsubone, Muneo Shoji, Masato Oikawa, Ryuichi Sakai

LIF - Molecular and Chemical Life Science

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

Abstract

An efficient total synthesis of dysiherbaine, a potent and subtype-selective agonist for ionotropic glutamate receptors, has been achieved. An advanced key intermediate in the previous synthesis of neodysiherbaine A and its analogues was selected as the starting point, and cis-oriented amino alcohol functionality on the tetrahydropyran ring was installed by using an intramolecular S_N2 cyclization of N-Boc-protected amino alcohol. The amino acid appendage was constructed by catalytic asymmetric hydrogenation of enamide ester.

Original language	English
Pages (from-to)	5697-5700
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	32
DOIs	https://doi.org/10.1016/j.tetlet.2007.05.180
Publication status	Published - 2007 Aug 6

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.05.180

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title = "Total synthesis of dysiherbaine",

abstract = "An efficient total synthesis of dysiherbaine, a potent and subtype-selective agonist for ionotropic glutamate receptors, has been achieved. An advanced key intermediate in the previous synthesis of neodysiherbaine A and its analogues was selected as the starting point, and cis-oriented amino alcohol functionality on the tetrahydropyran ring was installed by using an intramolecular SN2 cyclization of N-Boc-protected amino alcohol. The amino acid appendage was constructed by catalytic asymmetric hydrogenation of enamide ester.",

author = "Makoto Sasaki and Nobuyuki Akiyama and Koichi Tsubone and Muneo Shoji and Masato Oikawa and Ryuichi Sakai",

note = "Funding Information: This work was financially supported by a Grant-in-Aid for Scientific Research on Priority Area {\textquoteleft}Creation of Biologically Functional Molecules{\textquoteright} (No. 16073202) from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.",

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doi = "10.1016/j.tetlet.2007.05.180",

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T1 - Total synthesis of dysiherbaine

AU - Sasaki, Makoto

AU - Akiyama, Nobuyuki

AU - Tsubone, Koichi

AU - Shoji, Muneo

AU - Oikawa, Masato

AU - Sakai, Ryuichi

N1 - Funding Information: This work was financially supported by a Grant-in-Aid for Scientific Research on Priority Area ‘Creation of Biologically Functional Molecules’ (No. 16073202) from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

PY - 2007/8/6

Y1 - 2007/8/6

N2 - An efficient total synthesis of dysiherbaine, a potent and subtype-selective agonist for ionotropic glutamate receptors, has been achieved. An advanced key intermediate in the previous synthesis of neodysiherbaine A and its analogues was selected as the starting point, and cis-oriented amino alcohol functionality on the tetrahydropyran ring was installed by using an intramolecular SN2 cyclization of N-Boc-protected amino alcohol. The amino acid appendage was constructed by catalytic asymmetric hydrogenation of enamide ester.

AB - An efficient total synthesis of dysiherbaine, a potent and subtype-selective agonist for ionotropic glutamate receptors, has been achieved. An advanced key intermediate in the previous synthesis of neodysiherbaine A and its analogues was selected as the starting point, and cis-oriented amino alcohol functionality on the tetrahydropyran ring was installed by using an intramolecular SN2 cyclization of N-Boc-protected amino alcohol. The amino acid appendage was constructed by catalytic asymmetric hydrogenation of enamide ester.

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DO - 10.1016/j.tetlet.2007.05.180

M3 - Article

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SP - 5697

EP - 5700

JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Total synthesis of dysiherbaine

Abstract

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